Cyclades Islands
The Cyclades
The Cyclades are the Greece you've always pictured: whitewashed villages clinging to cliffsides, cobblestone lanes winding toward the sea, and that iconic blue-and-white architecture that never gets old. But beyond the postcards, each island has a distinct personality waiting to be discovered.
Longer sailing distances and more open water make this our more adventurous route. The reward? Some of the most stunning scenery in the Mediterranean, where every island feels like a completely different world.
A note on safety: Because of the possibility of rough seas, we are only able to offer these routes from Athens if the weather permits. Your skipper will have an accurate forecast when you arrive and will make the final decision. Safety is our number one priority.
3–6 Hours
Sailing Time Between Islands
Occasional Rough Seas
Winds & Sea Conditions
White-Washed
Architecture
Don't Miss
Breathtaking views from a rooftop bar in Serifos
Take a private guided tour of Kythnos with local expert George Vadivoulis (your captain can help set this up)
Swim & snorkel right from your yacht in Paros
Kea
The serene gateway to the Cyclades, Kea is blessed with rugged hills, secluded beaches, and lush valleys filled with oak trees. Its capital, Ioulis, is a traditional hilltop village with winding alleys and panoramic views.
Highlights
- ◆Hiking to the ancient city of Karthea
- ◆Snorkeling or scuba diving among shipwrecks like HMHS Britannic
- ◆Relaxing at secluded beaches such as Xyla and Spathi
- ◆Sampling renowned local thyme honey at village shops
Historical Landmarks
- ◆Ancient Karthea ruins
- ◆Lion of Kea
Hidden Gems
- ◆Festival of Agia Marina (July) – Traditional celebration with local music and food
- ◆Pisses Valley – Scenic hiking trails with ancient pathways and oak trees
- ◆Local Honey Producers – Taste authentic thyme honey from family-owned apiaries
Kythnos
Kythnos remains wonderfully authentic, known for its natural hot springs, charming whitewashed villages, and over 90 beaches, many accessible only by boat.
Highlights
- ◆Relaxing in Loutra's seaside thermal hot springs
- ◆Anchoring at Kolona Beach's unique double-sided bay
- ◆Exploring Dryopida village and its spectacular Katafiki Cave
- ◆Enjoying local cheese dishes and baked pies
Historical Landmarks
- ◆Katafiki Cave
- ◆Historical trails connecting ancient settlements
Hidden Gems
- ◆Panagia Kanala – Pine-covered monastery overlooking quiet beaches
- ◆Traditional Pottery Workshops – Visit artisans in Dryopida crafting pottery
- ◆Thermiotiko Cheese Tasting – Sample this distinctive local cheese in village tavernas
Syros
Syros, capital of the Cyclades, combines elegant neoclassical architecture and vibrant cultural life with serene beaches and charming villages.
Highlights
- ◆Strolling through the historic alleys of Ano Syros
- ◆Swimming beneath mansions at Vaporia's picturesque sea platforms
- ◆Discovering Grammata Bay's ancient sailors' inscriptions
- ◆Tasting San Michali cheese and sweets in Ermoupoli's markets
Historical Landmarks
- ◆Apollo Theater
- ◆Saint George Cathedral
- ◆Ano Syros medieval quarter
Hidden Gems
- ◆Rebetiko Music Evenings – Experience live music sessions in Ano Syros tavernas
- ◆San Michali Cheese – Visit local markets to taste this rare, aged cheese
- ◆Agios Stefanos Chapel – Secluded seaside chapel accessible by boat or hike
Serifos
Serifos captivates sailors with its dramatic landscape of golden cliffs, countless hidden coves, and quiet beaches. Its hilltop Chora cascades down the slope like a white waterfall.
Highlights
- ◆Hiking to the fascinating abandoned mines at Megalo Livadi
- ◆Swimming at pristine Psili Ammos beach, one of Greece's most beautiful
- ◆Exploring the cliffside chapel and twin coves at Agios Sostis
- ◆Tasting rare underground-aged Lakkou cheese
Historical Landmarks
- ◆Megalo Livadi Mining Museum
- ◆Chora's Venetian castle ruins
- ◆Gria Castle
Hidden Gems
- ◆Agios Sostis Cove – Twin turquoise coves and cliffside chapel
- ◆Local Lakkou Cheese – Aged underground cheese unique to Serifos
- ◆Mining Museum – Small museum detailing Serifos' fascinating mining history
Paros
Paros perfectly blends Cycladic beauty, historical depth, and vibrant village life. While its main towns bustle with energy, hidden trails and quiet coves await exploration.
Highlights
- ◆Hiking the Byzantine Road from Lefkes to Prodromos
- ◆Anchoring at turquoise lagoons around Panteronisia islets
- ◆Visiting ancient marble quarries at Marathi
- ◆Sampling local Parian cheeses and seafood in charming seaside tavernas
Historical Landmarks
- ◆Church of Panagia Ekatontapiliani
- ◆Ancient marble quarries of Marathi
- ◆Venetian fortress ruins in Naoussa
Hidden Gems
- ◆Aliki's Abandoned Hotel – Open-air graffiti art gallery amidst abandoned ruins
- ◆Pirate Festival (Naoussa) – Colorful re-enactment event each August
- ◆Routes in Marpissa Festival – A charming traditional arts and culture festival
Sifnos
Known as the culinary heart of the Cyclades, Sifnos is famed for its gastronomy, pottery, and pristine landscapes dotted with whitewashed chapels.
Highlights
- ◆Walking to the dramatic Church of Seven Martyrs near Kastro
- ◆Visiting traditional pottery workshops in Artemonas
- ◆Relaxing on the remote Fikiada Beach, accessible only by hike or boat
- ◆Participating in local summer panigiri festivals
Historical Landmarks
- ◆Ancient village of Kastro
- ◆Chrysopigi Monastery
- ◆Prophet Elias Monastery
Hidden Gems
- ◆Summer Panigiri Festivals – Vibrant community celebrations with local food and music
- ◆Manoura Cheese – Rare goat cheese uniquely aged in wine sediment
- ◆Decorative Pottery Chimneys – Unique ceramic rooftop art found throughout island villages
Naxos
Naxos, the largest Cycladic island, blends lush landscapes, mountainous terrain, and historical wonders with endless beaches. It is also home to our Cedar Forest Villa.
Highlights
- ◆Hiking to the summit of Mount Zas for expansive views
- ◆Exploring Apeiranthos, famed for its marble streets and artisan traditions
- ◆Snorkeling at the spectacular Rina Sea Cave
- ◆Visiting the cedar forest and abandoned art-covered hotel at Aliko
Historical Landmarks
- ◆Temple of Apollo (Portara)
- ◆Temple of Demeter
- ◆Ancient Kouros statues near Apollonas and Melanes
Hidden Gems
- ◆Vallindras Kitron Distillery – Historic citron liqueur distillery in Halki village
- ◆Koronos Emery Mines – Exploring remnants of Naxos' unique emery-mining heritage
- ◆Matina & Stavros Tavern (Koronos) – Exceptional local mountain dining experience
Antiparos
Antiparos offers sailors a refined, laid-back escape—an island famed for its understated charm, hidden coves, and crystal-clear waters.
Highlights
- ◆Exploring the impressive stalactites of Antiparos Cave
- ◆Sailing to the archaeological treasures and secluded beaches on Despotiko Island
- ◆Snorkeling in the hidden sea caves of Fokospilies
- ◆Cycling quiet backroads to discover isolated coves
Historical Landmarks
- ◆Antiparos Cave (with inscriptions from ancient times)
- ◆Sanctuary of Apollo on Despotiko Island
Hidden Gems
- ◆Feast of Agia Marina (July) – A lively local festival with traditional music, food, and dancing
- ◆Cine Oliaros Open-Air Cinema – Charming movie nights beneath the stars
- ◆Secret Beaches near Faneromeni – Hidden, tranquil beaches known only to locals
7-Day Itinerary
A suggested week-long route through the Cyclades. Your captain will customize based on weather, wind, and your preferences.
What Our Guests Say
“Five friends and I set sail on the Lagoon 380 following the Saronic Gulf route and made unforgettable memories. It was the perfect mix of active adventure and relaxation. Our wonderful captain got to know each of us, listened to our requests, and tailored recommendations so we could fit the most fun into our days.”
Anthony A.
Friends · TripAdvisor
“This trip was hands down the best vacation we have ever done! The boat itself (Saona 47) was beautiful, comfortable, and offered a ton of different places to enjoy time on the water. The highlight was our captain and hostess — they listened to what we wanted and designed a great itinerary. The food exceeded our expectations at every single meal.”
Dave W.
Couples · TripAdvisor
“From start to finish, our sailing trip was nothing short of magical. We spent our days swimming in crystal-clear coves, wandering charming villages, and eating the most delicious local food. The crew struck the perfect balance of professionalism and laid-back Greek hospitality, making us feel completely at home.”
Molly K.
· TripAdvisor
Ready to Sail the Cyclades?
Contact us to plan your dream Cyclades sailing itinerary. We'll design the perfect route based on your dates, group size, and interests.
CHECK AVAILABILITY